There is an ongoing need in the fragrance industry to provide new chemicals to give perfumers and other persons the ability to create new fragrances for perfumes, colognes and personal care products.
The odor of musk is a universally appreciated fragrance and is usually thought of as the animal note in perfumes. A number of naturally occurring species, both of animal and vegetable origin, possess musk odors; however, only the animal sources have achieved any commercial importance. It is because of the high demand, short supply, and expensive cost of these naturally occurring musk odorants that numerous attempts have been made, since the 1920's to synthesize compounds which would duplicate these desirable odors. It has been long and well known that macrocyclic carbonyl compounds having more than 13, but fewer than 19, carbon atoms are involved in achieving a musk odor (See, U.S. Pat. No. 6,326,349).
For example, Mookherjee, et al., U.S. Pat. No. 3,718,696, disclose the preparation of a mixture of Muscone (3-methyl-1-cyclopentadecanone, Formula I) and α-methyl-cyclopentadecanone (Formula II) (1973).

Komatsu, et al., U.S. Pat. No. 3,923,699, disclose Ambretone (or Velvione) (cyclohexadecenone-5, Formula III) (1975).

Calderon, U.S. Pat. No. 3,935,270, describes previously reported macrocyclic musk ketones including Civetone (9-cycloheptadecenone-1, Formula IV), Dihydrocivetone (cycloheptadecanone, Formula V), and Exaltone (cyclopentadecanone, Formula VI) (1976).



More recently, Nobuhiro, et al., U.S. Pat. No. 6,057,372, disclose Animusk (or Globanone) (8-cyclohexadecen-1-one, Formula VII) (2000).

Helmlinger, et al., U.S. Pat. No. 6,326,349, disclose Cosmone (3-methyl-cyclotetradec-5-en-1-one, Formula VIII) (2001).

Reckziegel, et al., U.S. Pat. No. 7,129,380, disclose Aurelione (a mixture of 7-cyclohexadecen-1-one, Formula IX, and 8-cyclohexadecen-1-one, Formula VII) (2006).

Skilled in the art appreciate that small structural differences such as the number of double bonds and their positions in the ring would result in macrocyclic ketones with distinctive fragrance properties in addition to the musky odor. These distinctive properties can be highly valuable. They allow perfumers to create perfumes with unique and distinguished characters. However, many of these distinctive properties can also be undesirable and, thus, would render the macrocyclic ketones not suited for perfume use despite the musky odor. Further, practical considerations such as synthesis may also prevent the use of various macrocyclic ketones in commercial fragrance applications (See, U.S. Pat. No. 6,200,254).
It is well recognized by the art that whether a given macrocyclic ketone possesses useful fragrance properties and whether its synthesis can be carried out at a commercial scale are unpredictable. It requires undue experimentation to develop a particular macrocyclic ketone that meets the criteria of applicability based on the general knowledge in the art. For these reasons, a continuous and extensive effort has been made throughout the decades to search for novel macrocyclic ketone molecules suitable for fragrance use that can be produced via an economical process.